CN104984664A - Method for preparing amino acid modified polyether sulfone hematodialysis membrane - Google Patents
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Abstract
The invention relates to the technology of hematodialysis membranes, and aims at providing a method for preparing an amino acid modified polyether sulfone hematodialysis membrane. The method comprises the steps that chloromethyl group polyether sulfone, polarity aprotic organic solvent and a micromolecule pore-forming agent are taken and mixed to be stirred and dissolved to obtain a uniform and stable membrane casting solution; vacuum standing and bubble removing are carried out, and a chloromethyl group polyether sulfone hollow fiber membrane is prepared through a dry/wet phase inversion method and then immersed in hot water; finally, immersing is carried out through an ethanol solution, and drying is carried out; the chloromethyl group polyether membrane is immersed in a sodium hydroxide water solution to be reacted; the chloromethyl group polyether membrane is immersed in hot water; finally, the chloromethyl group polyether membrane is immersed in the ethanol solution, drying is carried out, and then the product is obtained. The chloromethyl group polyether sulfone hollow fiber membrane serves as a precursor material, and precise and controllable amidogen acidification modification can be carried out on the chloromethyl group polyether sulfone membrane through the electrophilic substitution policy. The polyether sulfone hematodialysis membrane modified through amino acid has the advantages of permanent hydrophilia, low-protein adsorbability and superior biocompatibility.
Description
Technical field
The present invention relates to haemodialysis membrane technology, particularly the low protein adsorption of one, the preparation method of the amino acid modified polyether sulphone hollow fibre film of biocompatibility excellence.
Background technology
Haemodialysis utilizes pellicle principle, and blood samples of patients and dislysate are incorporated into dialyzer simultaneously, in the reverse flow of dialysis membrane both sides, by means of the concentration gradient of pellicle both sides solute, removes toxin by diffusion.By moisture unnecessary in infiltration purged body, the harmful substance in blood is made to enter into dislysate by dialysis membrane.And again flow back to human body again through the blood of dialysing, and the utility that supplementary needed by human body is wanted, keep electrolyte balance and the acid-base balance of blood.Find out that dialysis membrane is the pith determining dialyzer performance thus.As a rule, hemodialysis membrane need possess higher toxin elimination efficiency, good biocompatibility, suitable water permeability, stable physics, chemical property, and not containing harmful material.
At present, clinical conventional hemodialysis membrane can be divided three classes: 1, cellulose membrane; 2, modification or regenerated cellulose film; 3, Polymer Synthesizing film.Wherein synthetic polymeric membrane mainly comprises the poly (ether sulfone) film of polyacrylonitrile film, polyvinyl alcohol film, PS membrane and the fragrant same clan.Polyacrylonitrile has good weatherability, good solvent resistance and chemical stability.In addition polyacrylonitrile and monomer whose acrylonitrile have objectionable intermingling, are easy to purify, and are conducive to purifying for extracorporeal blood.Polyacrylonitrile has been made hollow-fibre membrane by the Asahi Kasei Corporation of Japan first, and for haemodialysis and hemodiafiltration.But polyacrylonitrile film also also exists more shortcoming, the fragility as film is comparatively large, and the water permeability of the sterilization of bad mechanical strength, non-refractory, dry state film obviously descends degradation.Polyvinyl alcohol is a kind of water-soluble polymer, therefore must carry out suitable copolymerzation with cross-linking to it in advance.Methyl acrylate, methyl methacrylate, acrylonitrile, ethene etc. are had with the monomer of its copolymerization.Kuraray Co., Ltd. of Japan successfully develops ethylene-vinyl alcohol copolymer anisotropic membrane, its outer fine and close, internal layer porous.The haemodialyser made with this film is to β
2microglobulin has very strong removal ability.Sulphur atom in polysulfones chemical constitution is in the highest oxidation valency, adds the existence of phenyl ring, makes it have good chemical stability, can carry out sterilization treatment at 128 DEG C, and can at 90 DEG C Long-Time Service, there is good pliability and good mechanical property.The asymmetric ps hollow fiber uf membrane of Amicom company of U.S. development has good mechanical performance, stable chemical performance, porosity advantages of higher.The Wei Gao blood purification Products Co., Ltd of China develops the polysulfones hemodialysis membrane of high flux and small throughput respectively.In recent years, blood compatibility is better, heat resistance is higher, the better polyether sulfone of solubility property is also often used as Hemodialysis Membrane Material.The most successful polyether sulfone hemodialysis membrane of current Commercialization application is produced by the Membrana company of Germany.But due to the hydrophobicity of polyether sulfone materials, in use have that residual blood coagulation amount is large, the easy shortcoming such as adhesion protein, thus need to carry out modification to improve the application of film at blood purification to poly (ether sulfone) film.Nowadays the method reported mainly comprises three major types: 1, this is modifies, namely carries out basis to poly (ether sulfone) film material modifies; 2, surface modification, by chemical graft method (adopting the technology such as ozone, UV-irradiation, plasma) at film surface grafting hydrophilic macromolecule or bioactive macromolecule; 3 blend methods, as blended polyethylene pyrrolidones, polyethylene glycol oxide-propylene oxide block polymers, bioactive macromolecule class.Wherein especially in the majority to report the method for blending and modifying.Patent CN200510020277.1 reports a kind of preparation method of bioactive macromolecule modified poly (ether-sulfone) hollow-fibre membrane, content relate to one and comprises hydrophobic molecule, the hemodialysis membrane of hydrophilic molecule composition, wherein hydrophobic molecule is polyether sulfone, hydrophilic molecule is bioactive macromolecule, modified poly (ether sulfone) film obtained by describing according to patent has the features such as good biocompatibility, flux is high, selection separation property is good, but this bioactive macromolecule is DNA and protein-based, the activation of complement in blood thus can be caused in the process used.Patent CN201110256230.0 reports a kind of preparation method adopting amphipathic three block copolymer blending modified polyether sulphone (PES) hollow-fibre membrane.Film prepared by describing according to patent has the features such as the blood compatibility of permanent hydrophilic, anti-protein contamination ability and excellence.Patent CN201210590594.7 reports a kind of preparation method adopting heparan polyurethane comixing modified poly (ether-sulfone) hollow-fibre membrane, and the film prepared by describing according to patent has stronger anticoagulant functions.Patent CN201410425668.0 reports a kind of employing polyaniline original position auto-dope modified poly (ether-sulfone) hollow-fibre membrane, and forms poly-zwitterionic high anti-soil type polyether sulfone blood purification and preparation method thereof by sulfonation process at material surface.Modified Membrane prepared by describing according to patent has lower each albuminoid non-specific adsorption.But due to adding of this kind of amphipathic three block copolymer, thus in the preparation process of film, the micron-scale phase separation between polyether sulfone and additive can be caused, and then cause film surface roughness, and the series of problems such as film mechanical strength.Patent CN201410084111.5 reports a kind of preparation method of nano modification hydroxy dioxetane titanium mixture blending modified polyether sulphone (PES) hollow-fibre membrane.Polyether sulphone hollow fibre film prepared by describing according to patent has good biocompatibility and blood compatibility, hydrophily and smoothness, and has higher clearance and ultrafiltrate coefficient.But due to this inorganic nano-particle and poly (ether sulfone) film, especially film surface, just, thus there is the major hidden danger come off from film surface in a kind of simple physical absorption in use procedure subsequently.
By the investigation to above-mentioned prior art, can find that a larger shortcoming is, for by the blended method of modifying improving poly (ether sulfone) film performance, no matter be add hydrophilic macromolecule polyalcohol, still there is the inorganic nano-particle of nanoscale, all likely discharge from poly (ether sulfone) film gradually in application afterwards, thus at drinking water, food, in the application of especially field of medicaments, bring problems; In addition not exclusively compatible due to additive and polyether sulfone, thus in the preparation process of film, also can bring larger difficulty to the regulation and control of membrane pore structure.
Summary of the invention
The technical problem to be solved in the present invention is, overcomes deficiency of the prior art, provides a kind of preparation method of amino acid modified polyether sulfone hemodialysis membrane.
For technical solution problem, solution of the present invention is:
A kind of preparation method of amino acid modified polyether sulfone hemodialysis membrane is provided, comprises the steps:
(1) preparation of chloromethyl polyether sulphone hollow fibre film:
1 ~ 3: 5 ~ 8: 1 ~ 3 take chloromethyl polyether sulfone, polar non-proton organic solvent and Small molecular pore former in mass ratio, after mixing at 25 ~ 85 DEG C stirring and dissolving 6 ~ 10 hours, obtain the casting solution of stable homogeneous; Vacuum standing and defoaming is also held in required spinning temperature 25 ~ 85 DEG C, chloromethyl polyether sulphone hollow fibre film is obtained by dry/wetting phase conversion method, then soak 5 ~ 10 hours in the hot water of 40 ~ 60 DEG C, except the Small molecular pore former in striping surface and duct and residual solvent; Finally by alcohol solution dipping 2 ~ 5 hours, dry at 60 DEG C, for subsequent use;
(2) amino acid modified:
Obtained chloromethyl poly (ether sulfone) film is immersed in pH value is 8 ~ 10, amino acid concentration is in the sodium hydrate aqueous solution of 0.1mol/L ~ 2.0mol/L, reacts 2 ~ 5 hours at 20 DEG C ~ 40 DEG C; Then soak 5 ~ 10 hours in the hot water of 40 ~ 60 DEG C, removing is adsorbed on the amino acid in film surface and fenestra; Finally by alcohol solution dipping 2 ~ 5 hours, dry at 60 DEG C.
In the present invention, the structure of the chloromethyl polyether sulfone described in step (1) is as follows:
In formula, x=160 ~ 200, y=2 ~ 40; The ratio of x: y is 1: 0.01 ~ 1: 0.2; Chloromethylation degree is 0.01 ~ 0.2.
In the present invention, the polar non-proton organic solvent described in step (1) is the one in dimethylacetylamide, dimethyl formamide or N ~ methyl pyrrolidone.
In the present invention, the Small molecular pore former described in step (1) is the mixture of organic molecule and inorganic soluble salt; Wherein, organic molecule is the one in the polyethylene glycol of isopropyl alcohol, butanols or molecular weight 400, and inorganic soluble salt is the one in lithium chloride, lithium nitrate or lithium perchlorate.
In the present invention, the amino acid described in step (2) is the one in neutral amino acid, acidic amino acid or basic amino acid.
Preferably, described neutral amino acid is the one in glycine, alanine, leucine, proline, threonine or tyrosine; Described acidic amino acid is the one in aspartic acid or glutamic acid; Described basic amino acid is the one in lysine, arginine or histidine.
Compared with prior art, beneficial effect of the present invention is:
The present invention is using chloromethyl polyether sulphone hollow fibre film as precursor material, and by the strategy of parental materials, amino acidifying chloromethyl poly (ether sulfone) film being carried out to controllable precise is modified.Be there is by amino acid modified rear polyether sulfone hemodialysis membrane the feature of the biocompatibility of permanent hydrophilic, low protein adsorption and excellence.
Detailed description of the invention
Below by embodiment, the preparation method of a kind of amino acid modified polyether sulfone hemodialysis membrane of the present invention is described in further detail.
Embodiment one
Step one:
(x is 200, y is 2 to take chloromethyl polyether sulfone 10% by mass fraction; Chloromethylation degree 1%, Hangzhou Xiaoshan Jiang Cheng Chemical Co., Ltd.), dimethylacetylamide 80%, isopropyl alcohol 5%, lithium chloride 5%, stirring and dissolving 10 hours at 25 DEG C, obtain the casting solution of stable homogeneous, vacuum standing and defoaming is also held in required spinning temperature 25 DEG C, prepares chloromethyl polyether sulphone hollow fibre film by dry/wetting phase conversion method; Soak 10 hours in the hot water of 40 DEG C subsequently, except the Small molecular pore former in striping surface and duct and residual solvent, finally by alcohol solution dipping 2 hours, dry at 60 DEG C, for subsequent use.
Step 2:
It is 8 that the chloromethyl poly (ether sulfone) film prepared in step (1) is immersed in pH, glycine concentration is in the sodium hydrate aqueous solution of 2.0mol/L, react 5 hours at 20 DEG C, soak 5 hours in the hot water of 60 DEG C subsequently, removing is adsorbed on the amino acid in film surface and fenestra, finally by alcohol solution dipping 2 hours, dry at 60 DEG C, get the long sample sets of 10 50cm and dress up a small hollow fiber film component for test.
Embodiment two:
Step one:
(x is 160, y is 40 to take chloromethyl polyether sulfone 30% by mass fraction; Chloromethylation degree 20%, Hangzhou Xiaoshan Jiang Cheng Chemical Co., Ltd.), dimethyl formamide 50%, butanols 10%, lithium perchlorate 10%, stirring and dissolving 6 hours at 85 DEG C, obtain the casting solution of stable homogeneous, vacuum standing and defoaming is also held in required spinning temperature 85 DEG C, by preparing chloromethyl polyether sulphone hollow fibre film with dry/wetting phase conversion method; Soak 5 hours in the hot water of 60 DEG C subsequently, except the Small molecular pore former in striping surface and duct and residual solvent, finally by alcohol solution dipping 5 hours, dry at 60 DEG C, for subsequent use.
Step 2:
It is 10 that the chloromethyl poly (ether sulfone) film prepared in step (1) is immersed in pH, aspartic acid concentration is in the sodium hydrate aqueous solution of 0.1mol/L, react 2 hours at 40 DEG C, soak 10 hours in the hot water of 40 DEG C subsequently, removing is adsorbed on the amino acid in film surface and fenestra, finally by alcohol solution dipping 5 hours, dry at 60 DEG C, get the long sample sets of 10 50cm and dress up a small hollow fiber film component for test.
Embodiment three:
Step one:
(x is 180, y is 20 to take chloromethyl polyether sulfone 20% by mass fraction; Chloromethylation degree 10%, Hangzhou Xiaoshan Jiang Cheng Chemical Co., Ltd.), the polyethylene glycol 15% of N ~ methyl pyrrolidone 50%, molecular weight 400, lithium nitrate 15%, stirring and dissolving 8 hours at 40 DEG C, obtain the casting solution of stable homogeneous, vacuum standing and defoaming is also held in required spinning temperature 40 DEG C, prepares chloromethyl polyether sulphone hollow fibre film by dry/wetting phase conversion method; Soak 8 hours in the hot water of 50 DEG C subsequently, except the Small molecular pore former in striping surface and duct and residual solvent, finally by alcohol solution dipping 3 hours, dry at 60 DEG C, for subsequent use.
Step 2:
The chloromethyl poly (ether sulfone) film prepared in step (1) to be immersed in concentration be pH is 9, lysine concentration is in the sodium hydrate aqueous solution of 1.0mol/L, react 3 hours at 30 DEG C, soak 8 hours in the hot water of 50 DEG C subsequently, removing is adsorbed on the amino acid in film surface and fenestra, finally by alcohol solution dipping 3 hours, dry at 60 DEG C, get the long sample sets of 10 50cm and dress up a small hollow fiber film component for test.
Embodiment four:
Step one:
(x is 180, y is 20 to take chloromethyl polyether sulfone 20% by mass fraction; Chloromethylation degree 10%, Hangzhou Xiaoshan Jiang Cheng Chemical Co., Ltd.), the polyethylene glycol 10% of N ~ methyl pyrrolidone 60%, molecular weight 400, lithium nitrate 10%, stirring and dissolving 8 hours at 40 DEG C, obtain the casting solution of stable homogeneous, vacuum standing and defoaming is also held in required spinning temperature 40 DEG C, prepares chloromethyl polyether sulphone hollow fibre film by dry/wetting phase conversion method; Soak 8 hours in the hot water of 50 DEG C subsequently, except the Small molecular pore former in striping surface and duct and residual solvent, finally by alcohol solution dipping 3 hours, dry at 60 DEG C, for subsequent use.
Step 2:
The chloromethyl poly (ether sulfone) film prepared in step (1) to be immersed in concentration be pH is 9, leucine concentration is in the sodium hydrate aqueous solution of 1.0mol/L, react 3 hours at 30 DEG C, soak 8 hours in the hot water of 50 DEG C subsequently, removing is adsorbed on the amino acid in film surface and fenestra, finally by alcohol solution dipping 3 hours, dry at 60 DEG C, get the long sample sets of 10 50cm and dress up a small hollow fiber film component for test.
Embodiment five:
Step one:
(x is 180, y is 20 to take chloromethyl polyether sulfone 20% by mass fraction; Chloromethylation degree 10%, Hangzhou Xiaoshan Jiang Cheng Chemical Co., Ltd.), the polyethylene glycol 10% of N ~ methyl pyrrolidone 60%, molecular weight 400, lithium nitrate 10%, stirring and dissolving 8 hours at 40 DEG C, obtain the casting solution of stable homogeneous, vacuum standing and defoaming is also held in required spinning temperature 40 DEG C, prepares chloromethyl polyether sulphone hollow fibre film by dry/wetting phase conversion method; Soak 8 hours in the hot water of 50 DEG C subsequently, except the Small molecular pore former in striping silk and residual solvent, finally by alcohol solution dipping 3 hours, dry at 60 DEG C, for subsequent use.
Step 2:
The chloromethyl poly (ether sulfone) film prepared in step (1) to be immersed in concentration be pH is 9, TYR concentration is in the sodium hydrate aqueous solution of 1.0mol/L, react 3 hours at 30 DEG C, soak 8 hours in the hot water of 50 DEG C subsequently, removing is adsorbed on the amino acid in film surface and fenestra, finally by alcohol solution dipping 3 hours, dry at 60 DEG C, get the long sample sets of 10 50cm and dress up a small hollow fiber film component for test.
The performance parameter of hollow-fibre membrane in each embodiment
Ultrafiltrate coefficient test condition: use ox blood to measure, protein concentration is 60g/L ± 5g/L, transmembrane pressure TMP=100mmHg, temperature 25 DEG C.
Removing speed test condition: velocity of blood flow (Q
b); Dialysate flow rate (Q
d) 500mL/min; TMP=100mmHg; Temperature 25 DEG C.The computing formula of removing speed is as follows:
Wherein C
0for solute initial concentration (mol/L); C
tfor solute concentration (mol/L) during sampling.
Claims (6)
1. a preparation method for amino acid modified polyether sulfone hemodialysis membrane, is characterized in that, comprise the steps:
(1) preparation of chloromethyl polyether sulphone hollow fibre film:
1 ~ 3: 5 ~ 8: 1 ~ 3 take chloromethyl polyether sulfone, polar non-proton organic solvent and Small molecular pore former in mass ratio, after mixing at 25 ~ 85 DEG C stirring and dissolving 6 ~ 10 hours, obtain the casting solution of stable homogeneous; Vacuum standing and defoaming is also held in required spinning temperature 25 ~ 85 DEG C, chloromethyl polyether sulphone hollow fibre film is obtained by dry/wetting phase conversion method, then soak 5 ~ 10 hours in the hot water of 40 ~ 60 DEG C, except the Small molecular pore former in striping surface and duct and residual solvent; Finally by alcohol solution dipping 2 ~ 5 hours, dry at 60 DEG C, for subsequent use;
(2) amino acid modified:
Obtained chloromethyl poly (ether sulfone) film is immersed in pH value is 8 ~ 10, amino acid concentration is in the sodium hydrate aqueous solution of 0.1mol/L ~ 2.0mol/L, reacts 2 ~ 5 hours at 20 DEG C ~ 40 DEG C; Then soak 5 ~ 10 hours in the hot water of 40 ~ 60 DEG C, removing is adsorbed on the amino acid in film surface and fenestra; Finally by alcohol solution dipping 2 ~ 5 hours, dry at 60 DEG C.
2. method according to claim 1, is characterized in that, the structure of the chloromethyl polyether sulfone described in step (1) is as follows:
In formula, x=160 ~ 200, y=2 ~ 40; The ratio of x: y is 1: 0.01 ~ 1: 0.2; Chloromethylation degree is 0.01 ~ 0.2.
3. method according to claim 1, it is characterized in that, the polar non-proton organic solvent described in step (1) is the one in dimethylacetylamide, dimethyl formamide or N ~ methyl pyrrolidone.
4. method according to claim 1, it is characterized in that, the Small molecular pore former described in step (1) is the mixture of organic molecule and inorganic soluble salt; Wherein, organic molecule is the one in the polyethylene glycol of isopropyl alcohol, butanols or molecular weight 400, and inorganic soluble salt is the one in lithium chloride, lithium nitrate or lithium perchlorate.
5. method according to claim 1, it is characterized in that, the amino acid described in step (2) is the one in neutral amino acid, acidic amino acid or basic amino acid.
6. method according to claim 5, it is characterized in that, described neutral amino acid is the one in glycine, alanine, leucine, proline, threonine or tyrosine; Described acidic amino acid is the one in aspartic acid or glutamic acid; Described basic amino acid is the one in lysine, arginine or histidine.
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| CN106310970A (en) * | 2016-09-23 | 2017-01-11 | 天津工业大学 | Modified polyvinylidene fluoride hollow fiber membrane for hematodialysis |
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